Alongside his older brother, Connor Maguire, Maguire is a prime mover in the conspiracy which leads to the outbreak of rebellion in Ireland on October 23, 1641. He is tasked with securing County Fermanagh for the rebels, but is only partially successful, with several key fortresses in the county, including Enniskillen Castle, remaining under Protestant settler control. His attempt to murder Sir William Cole immediately prior to the rising fails, but the landowner Arthur Champion is killed in one of the first actions of the rebellion. In November 1641, he joins Felim O’Neill of Kinard at Newry to issue a proclamation in which the rebels claim they are acting in defence of King Charles and Catholicism. In December 1641, the Fermanagh army under Maguire slaughters many of the garrison and refugees in Tully Castle, apparently in retaliation for the killing of the garrison of a Maguire castle which had been taken by assault some days previously. He also destroys Castle Archdale and its neighbouring settler village, and kills eight Protestant settlers at Monea Castle. In early 1642, he is expelled from the Irish Parliament and in the summer of the same year he is made a colonel in Owen Roe O’Neill‘s army in Ulster.
Maguire is appointed Governor of Fermanagh by the authorities of the newly established Confederate Ireland. He commands the rebel reserve in the Battle of Benburb in June 1646. He leads raids into Protestant-held areas in east Ulster, before joining O’Neill in his campaigns in Leinster in the autumn of 1646. Later that year, he raids lands in Connacht controlled by the Royalist commander, Ulick Burke, 1st Marquess of Clanricarde. In August 1647, O’Neill and Maguire move the army to Leinster, where Maguire quarrels so vigorously with O’Neill over the payment of troops that the general orders his arrest and court-martials him. After the court-martial, Maguire and his supporters, about five or six regiments, draw up their forces and threaten to desert. The mutiny soon dissipates and Maguire remains allied to O’Neill.
In 1648, Maguire joins O’Neill in opposing the truce between the Confederates and Royalists. He plays a prominent role in the skirmishes and evasive manoeuvrings that occur between the two sides in central Ireland. In the winter of 1648, Maguire withdraws north and on November 13 he is killed while leading an attack on a fortress near Jamestown, County Leitrim.
The assault focuses on the English fort which sits at a bridge on the River Blackwater, marking the border between Counties Tyrone and Armagh. It is built by Walter Devereux, 1st Earl of Essex, in 1575 as an outpost of English military strength in the heart of Gaelic Ulster, but also to secure the power of the main Irish ally in the region, Hugh O’Neill, Baron of Dungannon. The fort is composed of a square earthwork bawn “twelve score yards in circuit” reinforced by two bulwarks and punctuated with gun loops in its ramparts. In one corner stands a wooden tower, four stories tall, topped with a wooden walkway and a slate-covered building. It is accessed by two doors, one leading out onto the ramparts, another leading to a cellar. Each story has defensive firing loops, also known as spike holes. This tower overlooks a road and bridge across the river. At the other side of the river, on the Tyrone side, is a stone tower. The stone tower controls access to the bridge, as the road runs through it via large wooden doors.
Hugh O’Neill, Lord of Tyrone, is thought an ally of the English Crown and he is supported by the English authorities in Dublin as a counterweight to the power of other native lords in Ulster such as Turlough Lynagh O’Neill. However, encroachment by English authorities on the liberties of the native Irish lords in Ulster during the 1580s and early 1590s causes O’Neill to create an alliance of Irish lords, which look to throw off English rule with the help of Philip II of Spain. From April 1593, O’Neill orchestrates a proxy war against the English using Hugh Maguire, Lord of Fermanagh, and Hugh Roe O’Donnell, Lord of Tyrconnell. They engage the English in the west of Ulster while O’Neill, outwardly still loyal to the Crown, strengthens his power base in Ulster and subdues the Crown’s Irish allies in the north. The Irish lay siege to Enniskillen Castle and defeat an English force sent to relieve it.
O’Neill’s alliance is not limited to Ulster as he is allied to Fiach McHugh O’Byrne in Leinster. He has come under increasing pressure from Lord DeputyWilliam Russell‘s military expeditions into the Wicklow Mountains. In desperation, Fiach McHugh asks that Tyrone offer help or at least raid the northern Pale to draw Russell out of Wicklow. O’Neill requests a meeting with Russell to discuss how to proceed but this is dismissed by the Lord Deputy as a ploy to draw him out of O’Byrne’s lands. Therefore, to help O’Byrne, O’Neill makes his first open move against the Crown.
On the morning of Sunday, February 16, 1595, Art MacBaron O’Neill approaches the fort from the direction of Armagh with 40 men, escorting what appears to be two prisoners. As they cross the bridge one of the English warders notices the match cords of the Irishmen’s matchlock calivers are lit, a sign that they are ready to fire. The English open fire and MacBaron’s men force their way into the stone tower, but the English withdraw to the upper stories and prevent the Irish from taking the tower. Meanwhile, on the other side of the river, 200 Irish soldiers sweep over the earth ramparts and take the bawn. The English soldiers and their families retreat to the wooden tower. Defensive fire from within keeps the Irish back and twice the warders thwart MacBaron’s attempts to burn the position. Fifteen of MacBaron’s men are killed attempting to storm the towers, and eight more later die of their wounds. The stalemate lasts until five o’clock in the evening when MacBaron calls for a ceasefire. He offers the garrison terms for their surrender. The English, led by Edward Cornwall, are critically low on ammunition but still prevaricate until MacBaron threatens to burn the fort to the ground with all in it. The ward’s surrender is agreed and MacBaron guarantees their safe passage to Newry.
The loss of the fort is doubtless a military setback for the Crown, but of more significance is the presence of the Earl of Tyrone in person. According to the English commander, O’Neill arrives after the surrender and is outraged at the losses suffered in taking the fort and is angry that the defenders had not been executed. After the English soldiers and their families leave, O’Neill looks on as the bridge is demolished and the fort’s defence slighted. Up until this point there is no concrete proof that O’Neill was active in the attacks by Maguire and O’Donnell in the west of Ireland. Now there is indisputable proof that the Crown was at war with O’Neill.
(Pictured: The Blackwater Fort at present-day Blackwatertown in County Armagh, built by the Earl of Essex during a foray into Ulster in 1575 and captured and destroyed by the Irish in 1595. This pen and ink sketch measures 22½ by 16½ inches and is dated March 27, 1587.)
As a young man O’Neill leaves Ireland, one of the ninety-nine involved in the Flight of the Earls escaping the English conquest of his native Ulster. He grows up in the Spanish Netherlands and spends 40 years serving in the Irish regiment of the Spanish army. He sees most of his combat in the Eighty Years’ War against the Dutch Republic in Flanders, notably at the Siege of Arras, where he commands the Spanish garrison. He also distinguishes himself in the Franco-Spanish War by holding out for 48 days with 2,000 men against a French army of 35,000.
O’Neill is, like many Gaelic Irish officers in the Spanish service, very hostile to the English Protestant presence in Ireland. In 1627, he is involved in petitioning the Spanish monarchy to invade Ireland using the Irish Spanish regiments. He proposes that Ireland be made a republic under Spanish protection to avoid in-fighting between Irish Catholic landed families over which of them would provide a prince or king of Ireland. This plot comes to nothing. However in 1642, He returns to Ireland with 300 veterans to aid the Irish Rebellion of 1641.
The subsequent war, known as the Irish Confederate Wars, is part of the Wars of the Three Kingdoms, civil wars throughout Britain and Ireland. Because of his military experience, O’Neill is recognised on his return to Ireland in July 1642, at Doe Castle in County Donegal, as the leading representative of the O’Neills and head of the Ulster Irish. Sir Phelim O’Neill resigns the northern command of the Irish rebellion in his favour and escorts him from Lough Swilly to Charlemont.
Jealousy between the kinsmen is complicated by differences between O’Neill and the Catholic Confederation which meet at Kilkenny in October 1642. O’Neill professes to be acting in the interest of Charles I, but his real aim is the complete Independence of Ireland as a Roman Catholic country, while the Old English Catholics represented by the council desire to secure religious liberty and an Irish constitution under the crown of England. More concretely, O’Neill wants the Plantation of Ulster overturned and the recovery of the O’Neill clan’s ancestral lands. Moreover, he is unhappy that the majority of Confederate military resources are directed to Thomas Preston‘s Leinster army. Preston is also a Spanish veteran but he and O’Neill have an intense personal dislike of each other.
Although O’Neill is a competent general, he is outnumbered by the Scottish Covenanter army that lands in Ulster in 1642. Following a reverse at Clones, he has to abandon central Ulster and is followed by thousands of refugees, fleeing the retribution of the Scottish soldiers for some atrocities against Protestants in the rebellion of 1641. He does his best to stop the killings of Protestant civilians, for which he receives the gratitude of many Protestant settlers. From 1642–1646 a stalemate exists in Ulster, which he uses to train and discipline his Ulster Army. This poorly supplied force nevertheless gains a very bad reputation for plundering and robbing friendly civilians around its quarters in northern Leinster and southern Ulster.
In 1646 O’Neill, with substantial Gallowglass numbers and additionally furnished with supplies by the Papal Nuncio, Giovanni Battista Rinuccini, attacks the Scottish Covenanter army under Major-General Robert Monro, who had landed in Ireland in April 1642. On June 5, 1646 O’Neill utterly routs Monro at the Battle of Benburb, killing or capturing up to 3,000 Scots. However after being summoned to the south by Rinuccini, he fails to take advantage of the victory, and allows Monro to remain unmolested at Carrickfergus.
In March 1646 a treaty is signed between James Butler, 1st Duke of Ormond and the Catholics, which would have committed the Catholics to sending troops to aid the Royalist cause in the English Civil War. The peace terms however, are rejected by a majority of the Irish Catholic military leaders and the Catholic clergy including the Nuncio, Rinuccini. O’Neill leads his Ulster army, along with Thomas Preston’s Leinster army, in a failed attempt to take Dublin from Ormond. However, the Irish Confederates suffer heavy military defeats the following year at the hands of Parliamentarian forces in Ireland at Dungan’s Hill and Knocknanauss, leading to a moderation of their demands and a new peace deal with the Royalists. This time O’Neill is alone among the Irish generals in rejecting the peace deal and finds himself isolated by the departure of the papal nuncio from Ireland in February 1649.
So alienated is O’Neill by the terms of the peace the Confederates have made with Ormond that he refuses to join the Catholic/Royalist coalition and in 1648 his Ulster army fights with other Irish Catholic armies. He makes overtures for alliance to George Monck, 1st Duke of Albemarle, who is in command of the parliamentarians in the north, to obtain supplies for his forces, and at one stage even tries to make a separate treaty with the English Parliament against the Royalists in Ireland. Failing to obtain any better terms from them, he turns once more to Ormond and the Catholic confederates, with whom he prepares to co-operate more earnestly when Oliver Cromwell‘s arrival in Ireland in August 1649 brings the Catholic party face to face with serious danger.
Before, however, anything is accomplished by this combination, O’Neill dies on November 6, 1649 at the O’Reilly stronghold of Cloughoughter Castle located on an island in Lough Oughter in County Cavan. There is no clear evidence of the cause of death, with one belief being that he was poisoned by a priest, while others think it is more likely that he died from an illness resulting from an old wound. Under cover of night he is reputed to have been brought to the Franciscan abbey in Cavan town for burial. However some local tradition still suggests that it may have been at Trinity abbey located upon an island in Lough Oughter, which may be more likely given the logistics of his removal. His death is a major blow to the Irish of Ulster and is kept secret for some time.
The Catholic nobles and gentry meet in Ulster in March 1650 to appoint a commander to succeed O’Neill, and their choice is Heber MacMahon, Roman Catholic Bishop of Clogher, the chief organiser of the recent Clonmacnoise meeting. O’Neill’s Ulster army is unable to prevent the Cromwellian conquest of Ireland, despite a successful defence of Clonmel by O’Neill’s nephew Hugh Dubh O’Neill and is destroyed at the Battle of Scarrifholis in County Donegal in 1650. Its remnants continue guerrilla warfare until 1653, when they surrender at Cloughoughter Castle in County Cavan. Most of the survivors are transported to serve in the Spanish Army.